Psychotropic Phenylisopropylamines derived from Apiole and Dillapiole

Abstract

IT is an interesting fact that most of the known psychotropic phenylisopropylamines (amphetamines) possess ring-substitution patterns identical to those of natural essential oils. (The single exception is the active 2-methoxy - 4,5 - methylenedioxyamphetamine (MMDA-2, IId¹); neither the allyl nor the propenyl counterpart has been observed in plant extracts.) Thus 3,4-methylenedioxyamphetamine (MDA, IIa) is related to safrole (Ia)² (Table 1), 3,4,5-trimethoxyamphetamine (TMA) to elemicin³, 3 - methoxy - 4,5 - methylenedioxyamphetamine (MMDA, IIc) to myristicin (Ic)⁴ (Table 1), 2,4,5-trimethoxy -amphetamine to asarone, and 2-methoxy-3,4-methylenedioxyamphetamine (MMDA-3a, IIb) to croweacin (Ib) (Table 1). C. F. Barfknecht, of Idaho University, tells us that there is preliminary evidence that these olefines may be aminated in the living organism, and this reaction can be readily performed in vitro. There are two additional essential oils known that contain the methylenedioxy ring. These are apiole (Ie) and dillapiole (If) (Table 1). These two naturally occurring aromatic ethers are the two possible ring-methoxylated analogues of myristicin.